Continuing our countdown of best and worst trades in Habs modern history, we have reached the 9th worst trade.

March 10, 1999: Montreal trades Mark Recchi to the Philadelphia Flyers for Dainius Zubrus and a 2nd round pick in the 1999 draft.

The 1998-99 season was a difficult one for the Montreal Canadiens. Struggling terribly to score goals and well on their way to missing the playoffs for only the second time since 1970, drastic changes began to take place. Already having shipped out starting goalie Jocelyn Thibault and veteran scorer Vincent Damphousse, General Manager Rejean Houle decided to move Recchi as well.

After having overpaid dearly to get Recchi from the Flyers only 4 years prior, Houle struck a deal to send Mark back where he came from. Looking to rebuild with youth, Houle grabbed the 21 year old Zubrus who had 8 points in 63 games with the Flyers at the time of the trade. Recchi on the other hand had 47 points with the Habs before the trade was made, enough points to have him still leading the Canadiens at season’s end. To further show how much the Habs were struggling to put the puck in the net at this point in their history, Martin Rucinsky led the team in goals with a paltry 17 on the year.

Zubrus has gone on to have a long and successful career in the NHL. Still playing with the New Jersey Devils, he has reached both the 1000 game and 500 point plateaus in his career. A massive centerman at 6’5 his scoring abilities never quite reached the potential that his first round selection called for.

The second round pick acquired by Montreal in the trade was used to select Matt Carkner. Carkner would not become an NHL regular for over ten years but found a home on the Ottawa Senators blueline for the past three seasons. A big and physical defender, he is better known for dropping the gloves than anything else and has played only 162 games in his career.

Recchi, unbeknownst to everyone in 1999, still had 11 productive NHL seasons in front of him. His first full season back in Flyers colors he scored 91 points, leading the team and bringing them all the way to the Conference Finals. He played 5 full seasons in his return with Philadelphia and led them in points on three separate occasions. Recchi returned to the team that drafted him in Pittsburgh following the lockout and continued his successful career. He was traded to the Carolina Hurricanes at the trade deadline in 2006 and would go on to win the Stanley Cup, knocking out the Canadiens in the process. A Canadiens team that was still searching for a point producing winger to play with Saku Koivu.

Five years later Recchi would still be playing at the age of 42. Now with the rival Boston Bruins, Mark would be playing the Habs in the first round of the playoffs once again. Still, 12 years after dealing away Recchi, Montreal finds a glaring hole on Scott Gomez’ wing. Stuck with a rotation of wingers such as Mathieu Darche, Travis Moen, Tom Pyatt and Benoit Pouliot playing alongside Gomez and Brian Gionta on the teams second line. Meanwhile Recchi is playing on the Bruins second line with Patrice Bergeron and Brad Marchand and playing well. Following a 48 point regular season at the age of 42, Recchi would once again help defeat Montreal in the playoffs en route to yet another Stanley Cup ring in 2011.

No one could have known in March of 1999 that Recchi would play and play well until he was 42 years old. But the reality is Montreal let go their best player at the time, a player who had over 250 goals left in him and were still being haunted by the deal 12 years later.